


Watch and learn, boy!

by ElenyasBlood



Category: Supernatural
Genre: Hand Jobs, M/M, Masturbation, Tender Sex, Underage Kissing, tender!Dean
Language: English
Status: Completed
Published: 2014-08-31
Updated: 2014-08-31
Packaged: 2018-02-15 12:11:24
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 2,785
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2228559
Author URL: https://archiveofourown.org/users/ElenyasBlood/pseuds/ElenyasBlood
Summary: <blockquote class="userstuff">
              <p>Sam seems to have trouble getting himself off. Dean finds a way to help!</p>
            </blockquote>





	Watch and learn, boy!

**Author's Note:**

> This is just shameless tender!Dean coaxing Sammy through his first real orgasm. uwu

Sam remembered when it happened for the first time. Dean had woken up with his boxers tented up, a small patch of dampness soaking the faded fabric where the tip of his penis was pressed against the seam.

“Why is it doing that?” Sam had asked, curiosity rising in his chest along with Dean's eyebrows.

“Doing what?”

Giggling, Sam had leaned in, reaching out to poke the hard flesh beneath his brother's boxers with his small fingers just to have Dean catch them up in his palm. “Why is it being... hard and big like that?”

There had been a dark pink flush creeping up the older boy's neck as he tried to come up with a proper reply, his fingers squeezing Sam's hand carefully. “It's because I'm a big boy and... sometimes it happens.”

“When?”

Dean had shrugged. “Now and then. Usually when I'm asleep or... when I wake up, I guess. Look, I don't know, it's... a big boy thing.”

Beaming, Sam had tried to wiggle his fingers out of his brother's grip, pink tongue poking out to nervously wet his lips. “Can I touch it?”

“What? _No_.” Dean's voice had sounded a little bit high-pitched by then, his clammy palm tightening around Sam's twitching hand. “Of course not. It's not a frigging _toy_.”

“But–“

“We're not gonna argue about this, Sammy. I won't let you touch it. It's... something private and you're... Just wait until you get old enough to have your own boner. And until then keep your eyes and fingers to yourself, would ya?”

Dean had hated to see his little brother's face fall, but the whole conversation tasted _wrongwrongwrong_ on his tongue and so he'd let go of Sam before hurriedly shimmying into his jeans.

“When will I be old enough, De?”

Eyes rolling, Dean had exhaled sharply. “Soon enough. Now go get your clothes and I'll see if I can find you some Lucky Charms, you little brat.”

And that had been the end of their conversation for the time being.

Time went on and so did the boys and though they never talked about it again, Sam eventually _did_ get his first hard-on at the age of thirteen and after a series of particularly confusing dreams.

Waking up at six o'clock in the morning, clammy sheets twisted around his legs and his hands still clenched in the pillow, he had felt a strange tingling sensation between his legs, like an itch he couldn't quite put his finger on. His cock had been strained, aching and touch-starved and there was a smoldering heat lingering right beneath his boxers, burning through his flesh and setting his skin on fire. Moaning, he'd tried to get rid of his condition, clumsily pawing at his crotch, and after a few minutes of fumbling and bucking his hips he'd spilled into his briefs, feeling sticky and flushed afterward.

It became a regular thing then. Sam would wake up with a boner and with his skin crawling he'd clasp his fingers around the twitching flesh, squeezing and rubbing clumsily until the tension would finally bleed out of him again. Biting his lips, he managed to spill most of the time, but even after a shuddering orgasm he'd feel somehow empty, unsatisfied and hungry.

Some nights, when Dean was already asleep, Sam would rut against the mattress, hips thrusting against the plush cushions until the tight, hot feeling dissolved.

Except Dean was never really asleep in those nights.

 ♦ 

They were stuck in Rufus' Cabin in Whitefish, Montana, two weeks before Sam's fifteenth birthday. John had left them earlier that week with nothing but a pile of canned food and a bag stuffed full of weapons and holy water. There were no books, no TV, no distraction of any kind, and after three days of staring out into the swampy green of the forest, Sam was ready to crawl up the walls. Rain was pelting down outside and after three futile attempts to pick a fight with his big brother, he decided it was time to go to bed.

Several hours and a shit-ton of water relentlessly clattering against the roof later, Sam awoke with a start. It was still pitch-black outside the fogged windows and with a groan the boy became aware of the increasing hardness between his thighs, his cock aching and leaking into his pajama bottoms. Streaks of pre-come already stained the soft fabric as Sam tugged the waistband up, snaking his hand beneath.

He still hadn't gotten used to the shape and weight of his cock. Slightly curved to the right side, it was hot and heavy in his palm, the tip tacky with pre-come and there was a bed of soft chestnut curls sprouting at the base. The skin was tight around the strained flesh, velvet-soft and sensitive to the touch, and Sam felt a moan forming in the back of his throat as he traced his thumb down the whole length. A shiver ran through his body and after another couple of slow, tentative touches, he became bolder, more desperate.

Rubbing and tugging, he moved his fingers down, trailing along the vein of the underside of his cock before following the curve up again, his hips cautiously bucking up the mattress as he bit his lips, carefully minding his brother sleeping in the same room. Sam was about to double his efforts in a needy attempt to get off, when he heard the creaking of rusty bed springs. Panicking, he felt a blush creep up his neck and chest and with a choked groan he pulled his hand up just in time to feel the mattress dip under his brother's weight.

“Dean? What are you–“

Dean's voice was low and heavy with slumber when he spoke, his breath warm against Sam's cheek. “Shh, it's all right, Sammy,” he whispered as he climbed under the covers with his brother, feet brushing along Sam's calves. “It's all right, you don't need to stop.”

“I, um, I'm s-sorry, Dean,” Sam mumbled, shuddering at the familiar feeling of Dean's bare skin against his, their legs intertwining tentatively. “I didn't mean to, um, wake you up.”

The low chuckle that ensued sent Sam reeling, his whole body involuntarily curling into his brother's as soon as they were both settled, their limbs cocooned into the clammy warmth of the blanket. “It's all good, Sammy. I was awake before you started having fun all by yourself.”

Sam felt himself choke on his breath and he was about to deny Dean's words when he felt the tip of a warm finger running along the seam of his worn shirt.

“Dean, what are y–“

But Dean's hand was already dipping past the frayed hem, trailing patterns on Sam's exposed belly. “Shhh, it's all right, little brother. I can help you.”

A shiver ran down Sam's back at the sensation of Dean gently tugging the soft curls of his happy trail and he barely managed to bite back a strangled moan, his hips bucking involuntarily. “How d-did you know?” he wheezed, voice rough.

“Heard you having trouble, Sammy. Want me to... to show you how to do it right?”

Gulping, Sam found himself nodding, and with a soft, shy smile curling his lips he locked eyes with his brother. Dean's fingers were warm when they traced the waistband of Sam's pajama bottoms, teasing the boy, making his pupils dilate and his breath going ragged. Their rhythm was almost playful, the soft touches sure, and Sam felt himself shuddering against his brother, his body squirming.

“Gotta take your time, Sammy,” Dean murmured, brushing his hand down the curve of Sam's cock, only one layer of thin, damp fabric separating their burning skin. “Gotta make it last, right?”

Nodding, Sam swallowed a lewd moan. Dean's fingers were wandering now, trailing down Sam's cock and softly squeezing his tensed balls through the fabric before running down his thighs, Dean's whole, calloused palm splayed on the creamy flesh. Dean took his time rubbing the smooth skin until it was all flushed.

“Make yourself all wet and ready before you start, yeah? Trust me, it'll make it so much better,” he whispered as pushed his mouth into the crook of Sam's neck, plush lips only inches away from the sensitive shell of the boy's ear. His fingers were now at the waistband again, thumbs toying with the frayed hem and a low chuckle forming in the back of his throat at the feeling of Sam's impatient movements towards him, those slim hips bucking and writhing beneath his grip.

“D-Dean, please,” Sam whined, toes curling into the sheets, kicking against the mattress. “I need... please...”

With a smile, Dean stilled his movements for just a second, savoring the moment, before he slowly began to push the strained sweats down his brother's lean body. “Shhh, easy, Sammy,” he cooed half-way through. “I'm here, 'm here.”

And Sam complied, his almost violent, bucking movements slowly easing as he let his brother drag down the damned fabric. His lower lip continued to quiver, spilling needy, little moans into the darkness.

Dean took his time getting rid of the pajama bottoms that had been riding low on his own hips once. Slowly he brushed his hands against his brother's long legs, feeling the smooth skin of his thighs, skimming up and down his flanks once the offensive clothing was gone. With his other arm securely wrapped around Sam's knobby shoulders, he cradled the boy with his whole body, pressing Sam flush against his chest to not miss a single shudder, not the slightest little tremor rolling through his little brother's body.

“You okay, Sammy? You good?” Dean asked after a few moments of deafening silence, his warm breath ghosting over Sam's ear and neck, sparking shivers in the dark.

Nodding frantically, Sam tried to push up again, feeling his brother's hand next to his twitching cock as a heavy weight, their scents and heat mingling beneath the sheets. “'M good, De.”

No further confirmation needed, Dean decided that he had had enough of the teasing and so did Sam, if his trembling body and the needy moan were any indication.

“Give me your hand,” he rasped as his fingers kept brushing through the damp curls in Sam's crotch. “C'mon, don't be shy. No need to anyway,” he continued as he felt Sam hesitating for the first time since their bodies had entangled under the blanket. But there was no shame in wanting to make yourself feel good and with a soft smile he told Sam so.

The boy's nod was slow and his lips curled into a lopsided smile, and he did as Dean had asked. A shiver ran down his spine as their fingers threaded together, Dean's broad palm cradling the back of his little brother's hand.

“There,” Dean murmured breathily, “now relax and just follow my movements. I'm gonna make you feel good, Sammy. I promise.” And with a deep exhale he clasped both their hands around Sam's cock, their fingers firmly squeezing the hot, strained flesh.

“G-god, Dean,” Sam moaned as soon as he felt the pressure, the heavy weight of their combined palms gripping his cock tight. “More.”

“Shhh, it's all right. You want to make sure you're ready to go first, huh?” Dean chuckled, moving their hands up in a leisurely pace, inching towards the leaking, pink tip. “C'mon, we're gonna do it together.”

And that they did. Rubbing Sam's palm across the sticky head of his cock, they slicked up the boy's palm and fingers thoroughly. Relentlessly, they brushed over the slit again and again, gathering all the glistening pre-come until each finger and every inch of Sam's hand was covered in sticky liquid.

Shuddering, the boy pressed closer to his big brother. “Dean, 's too much,” he whined, his lips quivering against Dean's jaw line as he pushed in.

“Nah, little brother, it's all right. You're good, trust me,” Dean murmured, taking in Sam's heady scent, the exciting mix of clean sweat and soap rushing through his lungs like an aphrodisiac. “Now, let's get started, shall we?”

Going slow, Dean moved their intertwined hands down Sam's cock, lazily dragging their fingers over the hot, slick length. It was easy, a familiar movement, practiced through lazy hours in motel rooms all over the country, and Sam's cock was beautifully shaped, slightly curved and long and thick. The skin was silken, hot like burning and smooth under their steadily moving hands.

Breathing labored, eyes fluttered shut and hips jerking desperately, Sam was already close to losing it after the first few strokes. He had never felt so strained, his nerve endings on fire. Sweat made his shaggy bangs stick to his forehead and with a shudder he chased the friction provided by their combined hands, currently squeezing the base of his cock.

“De, please,” Sam whimpered, tilting his head back to expose the long expanse of his neck. The pale column of his throat was like an invitation to Dean and the older boy dipped in, licking a long, hot stripe down his brother's neck.

Pressing a soft kiss into the hollow below his brother's throat, Dean twisted their wrists. “Shhh, it's okay, Sammy. Relax,” he managed to pant before feeling a pair of soft, wet lips trailing along his jaw.

Sam's breath was warm and smelled like mint toothpaste and sleep as he exhaled sharply. “Dean, can I...” he trailed off, whining. With their combined hands jacking him off, their pace still agonizingly slow and his body almost vibrating out of his skin, Sam's mouth felt incredibly empty. Not knowing what else to do, he pressed it against Dean's like they had done when they were children only this time he hesitantly parted his lips at the sensation of plush, warm flesh.

Their kiss was just as sweet and slow as their movements. With their hands twisting and tracing the beads of tacky pre-come spilling down Sam's cock, their tongues moved just as lazily. Sliding together, chasing each other's taste, licking deep before trailing a slick path down their chins and necks and the world was spiraling down, narrowing down on nothing but the feeling of their combined heat beneath the covers.

“Dean, _Dean_ ,” Sam wheezed, throat tight and voice incredibly rough in his big brother's ear. “'M close, I think.”

Humming quietly, Dean picked up their pace, fingers only slightly guiding his little brother's hands now. His own cock was painfully hard in his sweatpants, a damp patch steadily growing bigger in the front, soaking the fabric. But tonight was all about Sam, about giving and cherishing and so Dean continued to press warm, tickling kisses down his brother's neck and throat, licking the sweat from his skin and moving their hands to the sensitive tip of Sam's cock.

It took Sam only a couple more thrusts and a knowing twist of Dean's wrist to tip him over the edge and with a shout the boy shot his load into the sheets, hot, sticky come spilling down their entangled fingers. Pulling soft little moans of pleasure out of his brother's chest, Dean stroked Sam through his orgasm, his other hand rubbing small, soothing circles in Sam's skin as he skimmed his fingers down the slim flanks, both brothers slowly coming down from their highs.

“Shhhh, easy. It's okay, Sammy, shhhhh,” Dean mumbled while rubbing his lips across the sensitive shell of Sam's ear. “I got ya, shhhh. You're fine.”

And Sam hummed and whined his agreement, erratic movements slowly stilling as he rode out his bliss. His hair and skin were sticky, his bangs drenched in sweat and despite the utter warmth Dean's body cradled him in, he shivered. The sheets felt clammy around their bodies.

“You okay?” Dean asked after a few minutes of breathless silence, nothing but the sound of their chests heaving against each other in the silence. He was still holding the boy close, fingers never stilling against the smooth skin.

Sam managed a nod, his smile small and timid. “I... Dean, um... I don't know-”

“Hey, how about getting some sleep, huh? It's still dark outside, buddy,” Dean cut in, his grip faltering a bit. A rush of air left his lungs and suddenly their position, and with it the familiar closeness between them, threatened to become awkward.

Letting his eye-lids droop, Sam nodded, snuggling closer. “Yeah, sounds good to me,” he breathed before leaning in for a soft, hesitant kiss, just a brush of lips against lips, their tongues meeting fleetingly.

“Thank you,” he whispered then, smiling sleepily as he pushed his naked body against Dean's, every inch of tacky, golden skin exposed to Dean's tender touch.

 


End file.
